Nitrogen → HCID 11358991, compound

HRID 1766303Notes

Reaction equation

HRID 1766303 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)[CH2:2][CH3:3].N1C=CC=CC=1.N#N.[NH2:22][C:23]1[CH:24]=[CH:25][C:26]2[O:30][N:29]=[CH:28][C:27]=2[CH:31]=1.C([O-])(O)=O.[Na+]>ClCCl>[O:30]1[C:26]2[CH:25]=[CH:24][C:23]([NH:22][S:10]([C:7]3[CH:8]=[CH:9][C:4]([CH2:1][CH2:2][CH3:3])=[CH:5][CH:6]=3)(=[O:12])=[O:11])=[CH:31][C:27]=2[CH:28]=[N:29]1

Participants

7

Reactant 5

HCID 947NitrogenHCID 1049PyridineHCID 516892Sodium BicarbonateHCID 27372224-N-Propylbenzenesulphonyl chlorideHCID 183734211,2-Benzoxazol-5-amine

Product 1

HCID 11358991HCID 11358991, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4n-propylbenzenesulphonyl chloride (171 mg, 0.783 mmol) in dichloromethane (4 mL).was added pyridine (150 μL, 1.86 mmol) and the mixture was stirred under. N2 for 5 min, after which time 5-amino-1,2-benzisoxazole (100 mg, 0.746 mmol) was added. The resulting mixture was stirred for 2 h at room temperature, then saturated NaHCO3 solution (10 mL) was added and the mixture was extracted into ethyl acetate (20 mL). The organic phase was washed with brine, dried (Na2SO4), filtered and evaporated to give a residue that was purified using flash chromatography to afford a white solid (170 mg, 72%), single spot at Rf 0.68 (1:1 hexane:ethyl acetate). mp 130.0-130.6° C., HPLC purity 99+% (tR 2.44 min in 10% water-acetonitrile). 1H NMR (CDCl3): δ 8.62 (1H, d, J=1.0 Hz), 7.60 (2H, d, J=8.4 Hz), 7.48 (2H, m), 7.19 (3H, m), 6.86 (1H, s, N−H), 2.58 (2H, t, J=7.5 Hz), 1.58 (2H, sextet, J=7.4 Hz), 0.88 (3H, t, J=7.4 Hz). LCMS: 315.14 (M−). FAB-MS (MH+, C16H16N2O3S): calcd 317.0960, found 317.0962.

Workup

  1. stirringThe resulting mixture was stirred for 2 h at room temperature
  2. extractionthe mixture was extracted into ethyl acetate (20 mL)
  3. washThe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give a residue that
  8. customwas purified

Sources & evidence

ORD record
ord-5c989720d1c84184a95c8cc1710594ae
Source dataset
uspto-grants-2007_06
Patent number
US07230020B2

Reaction notes

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